The Financial Times' John Gapper weighs in with a new and elegant solution to the riddle that is deadbeat photographer Annie Leibovitz's descent into insolvency: Rich art collectors have no interest in buying her photographs, because they're not that good.

Readers will recall that Leibovitz, who earns a reported $2 million salary from Vanity Fair and pulls in $250,000 a day for commercial work, went into hock to the tune of $15 million two years ago to a shadowy high-end artshark firm called Art Capital Group. The impetus for the borrowing was reportedly a real estate mess she found herself in after workers renovating her Greenwich Village townhouse accidentally damaged the neighboring unit, causing her to have to buy and repair it at great cost. Two years and a handful of lawsuits later, that debt—which was collateralized with the rights to Leibovitz's photographs and her homes in Manhattan and upstate New York—had metastasized to $30 million and bankruptcy loomed.

Annie Leibovitz, perhaps the highest-paid celebrity photographer in the world, is profoundly broke. …
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You'd think an internationally known and highly compensated photographer with as many rich friends as Leibovitz ought to be able to retire such a debt quietly and without too much rancor, but Leibovitz seems to have been unable to make much of a dent. The plan with Art Capital was to sell off exclusive "Master Sets" of her prints for $3.5 million each. That didn't work out, and Art Capital sold off the debt to Colony Capital, New York real estate firm, in March. Colony's plan? Sell off exclusive "Master Sets" of her prints for $3.5 million each.

Deadbeat celebrity photographer Annie Leibovitz has a new debt collector to hide from: Art Capital…
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So how's it working out? It's unclear how many sets Leibovitz has managed to sell—the New York Times reported that three had been sold, at discounts, as of last December—but Gapper explains that she is simply not a high-earner when it comes to art photography:

[D]espite all her celebrity and talent, Leibovitz lacks earning power as an artist.

If she could sell her prints in galleries or at auction for as much as former fashion and society photographers such as Herb Ritts, Bettina Rheims and Richard Avedon – let alone contemporary artists who work in photography, such as Cindy Sherman, Richard Prince, Andreas Gursky and Gilbert & George – her financial worries would ease.

So far, she has not. The most that one of her photographs has fetched at public auction, according to Artnet, the online auction house, is £31,200. That was paid in 2005 for a signed print of a 1986 photograph of the (now dead) artist Keith Haring, naked and daubed with paint. Most of her prints auctioned this year have fetched in the single-figure thousands of dollars, and some in the hundreds.

Ouch. It's not entirely that collectors find Leibovitz's portfolio too commercial or focused on shallow celebrity, Gapper writes. It's also that Leibovitz has consistently failed, throughout her career, to sufficiently kiss the asses of the sort of people who would spend $3.5 million on a bunch of photographic prints. "She had very little interest in the art world for most of her career," a gallery owner who used to rep Leibovitz told Gapper. "She suffered from not caring about it, not paying enough attention."

And, as Andrew Goldman pointed out in a New York profile last year, Leibovitz was such an organizational basketcase that she couldn't be bothered to do little things like sign prints so that her agents could sell them for tens of thousands of dollars. "We dropped her because it would take six months just to get a print signed," one gallery owner told Gapper. "I've got one of her prints of Steve Martin sitting here that I hope to get signed soon instead of waiting for months. You have to set aside half a day a month to sign if you are serious about it –- that is paid time."